Direct α‑Functionalization of Simple Aldehydes via Oxidative N‑Heterocyclic Carbene Catalysis

Direct α‑Functionalization of Simple Aldehydes via Oxidative N‑Heterocyclic Carbene Catalysis

A direct α-functionalization of simple aldehydes under N-Heterocyclic Carbene (NHC) catalysis and direct generation of ester enolate equivalents from nonfunctionalized aldehydes are disclosed. The catalysis involves selective enolate generation from an oxidatively generated NHC-bounded ester interme...

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Veröffentlicht in:Organic letters 2013-01, Vol.15 (1), p.50-53
Hauptverfasser: Mo, Junming, Yang, Ruojie, Chen, Xingkuan, Tiwari, Bhoopendra, Chi, Yonggui Robin
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Catalysis
Heterocyclic Compounds - chemistry
Ketones - chemistry
Methane - analogs & derivatives
Methane - chemistry
Molecular Structure
Oxidation-Reduction
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Zusammenfassung:A direct α-functionalization of simple aldehydes under N-Heterocyclic Carbene (NHC) catalysis and direct generation of ester enolate equivalents from nonfunctionalized aldehydes are disclosed. The catalysis involves selective enolate generation from an oxidatively generated NHC-bounded ester intermediate as a key step. The ester enolate intermediates undergo stereoselective reactions with enones and trifluoromethyl ketones.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol303035r